In 2014 New Perspectives Theatre Company staged the first adaptation on the stage of a short story by Saul Bellow, “Him with His Foot in His Mouth.” The changes made to the story in its adaptation for the stage inform our understanding of the comic effect of the story, particularly in relation to the different endings involved. The dynamic of the story depends upon the deployment of two different concepts of comedy — as the expression of an aggressive, materialistic society (Freud, The Joke in Relation to the Unconscious)or as a means of reforming society in green comedy (Northrop Frye, The Anatomy of Criticism). The story focusses upon the legitimate irresponsibility of comedy, and on the relation of comedy to freedom, defending it as a social and even a sacred good. The one-liners uttered by the hero exemplify comedy of a corrective nature, offering a healthy critique of social behavior, particularly in terms of the relation of art to money, and contest Freud’s theory as tainted by its social context and economic basis.